CA2398898A1 - Therapeutic or preventive agent for digestive system diseases containing a diaminotrifluoromethylpyridine derivative - Google Patents
Therapeutic or preventive agent for digestive system diseases containing a diaminotrifluoromethylpyridine derivative Download PDFInfo
- Publication number
- CA2398898A1 CA2398898A1 CA002398898A CA2398898A CA2398898A1 CA 2398898 A1 CA2398898 A1 CA 2398898A1 CA 002398898 A CA002398898 A CA 002398898A CA 2398898 A CA2398898 A CA 2398898A CA 2398898 A1 CA2398898 A1 CA 2398898A1
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- CA
- Canada
- Prior art keywords
- group
- substituted
- alkyl
- phenyl
- therapeutic
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 208000010643 digestive system disease Diseases 0.000 title claims abstract 10
- 230000003449 preventive effect Effects 0.000 title claims abstract 10
- 230000001225 therapeutic effect Effects 0.000 title claims abstract 10
- UVPXDGMMAFWHMJ-UHFFFAOYSA-N 2-(trifluoromethyl)pyridine-3,4-diamine Chemical class NC1=CC=NC(C(F)(F)F)=C1N UVPXDGMMAFWHMJ-UHFFFAOYSA-N 0.000 title claims abstract 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 16
- 239000003795 chemical substances by application Substances 0.000 claims abstract 9
- 125000003342 alkenyl group Chemical group 0.000 claims abstract 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract 6
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract 6
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 4
- 125000000304 alkynyl group Chemical group 0.000 claims abstract 3
- 239000004480 active ingredient Substances 0.000 claims abstract 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract 2
- 125000002950 monocyclic group Chemical group 0.000 claims abstract 2
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims abstract 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract 2
- 125000003367 polycyclic group Chemical group 0.000 claims abstract 2
- 125000004585 polycyclic heterocycle group Chemical group 0.000 claims abstract 2
- 150000003839 salts Chemical class 0.000 claims abstract 2
- 229910052717 sulfur Inorganic materials 0.000 claims abstract 2
- 125000004434 sulfur atom Chemical group 0.000 claims abstract 2
- 125000001188 haloalkyl group Chemical group 0.000 claims 9
- 125000005843 halogen group Chemical group 0.000 claims 7
- -1 indanylcarbonyl group Chemical group 0.000 claims 5
- 125000001544 thienyl group Chemical group 0.000 claims 4
- 125000002541 furyl group Chemical group 0.000 claims 3
- 125000005090 alkenylcarbonyl group Chemical group 0.000 claims 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims 2
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims 2
- TUWCZRFHNIOVTC-UHFFFAOYSA-N fuzapladib Chemical group CCS(=O)(=O)NC1=NC=C(C(F)(F)F)C=C1NC(=O)C1CCCCC1 TUWCZRFHNIOVTC-UHFFFAOYSA-N 0.000 claims 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims 2
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 claims 2
- ADFXYFXTVPPANT-UHFFFAOYSA-N 3-fluoro-n-[2-(propan-2-ylsulfonylamino)-5-(trifluoromethyl)pyridin-3-yl]benzamide Chemical compound CC(C)S(=O)(=O)NC1=NC=C(C(F)(F)F)C=C1NC(=O)C1=CC=CC(F)=C1 ADFXYFXTVPPANT-UHFFFAOYSA-N 0.000 claims 1
- OXNVUDNVKDMBBJ-UHFFFAOYSA-N 4-fluoro-n-[2-(methanesulfonamido)-5-(trifluoromethyl)pyridin-3-yl]benzamide Chemical compound CS(=O)(=O)NC1=NC=C(C(F)(F)F)C=C1NC(=O)C1=CC=C(F)C=C1 OXNVUDNVKDMBBJ-UHFFFAOYSA-N 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims 1
- 125000000262 haloalkenyl group Chemical group 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- SHZCBLZEPOLJSZ-UHFFFAOYSA-N n-[2-(methanesulfonamido)-5-(trifluoromethyl)pyridin-3-yl]furan-2-carboxamide Chemical compound CS(=O)(=O)NC1=NC=C(C(F)(F)F)C=C1NC(=O)C1=CC=CO1 SHZCBLZEPOLJSZ-UHFFFAOYSA-N 0.000 claims 1
- LDVBXVUZGLSFBY-UHFFFAOYSA-N n-[2-(propan-2-ylsulfonylamino)-5-(trifluoromethyl)pyridin-3-yl]cyclopentanecarboxamide Chemical compound CC(C)S(=O)(=O)NC1=NC=C(C(F)(F)F)C=C1NC(=O)C1CCCC1 LDVBXVUZGLSFBY-UHFFFAOYSA-N 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
Landscapes
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyridine Compounds (AREA)
Abstract
A digestive system disease therapeutic or preventive agent containing as an active ingredient a diaminotrifluoromethylpyridine derivative represented by the formula (I) or its salt:
(see formula I) wherein X is a -CW1R1 group, a -COCOR2 group, a -CW1NHCOR2 group, a -C(=W1)W2R3 group or a -CW1N(R4)R5 group; Y is an alkyl group, a -CW3R6 group, a -COCOR7 group, a -NHCOR7 group, a -C(=W3)W4R5 group, a - (NH)m SO2R9 group, a -(NH)m SO2OR10 group or a - (NH)m SO2N(R11)R12 group; each of R1, R6 and R9 is a chain hydrocarbon group, a monocyclic hydrocarbon group, a polycyclic hydrocarbon group, a monocyclic heterocycle group or a polycyclic heterocycle group; each of R2 and R7 is an alkyl group, an alkoxy group, a phenyl group or a phenoxy group; each of R3, R8 and R10 is an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, a phenyl group or a benzyl group; each of R4, R5, R11 and R12 is an alkyl group; each of W1, W2, W3 and W4 is an oxygen atom or a sulfur atom;
and m is 0 or 1.
(see formula I) wherein X is a -CW1R1 group, a -COCOR2 group, a -CW1NHCOR2 group, a -C(=W1)W2R3 group or a -CW1N(R4)R5 group; Y is an alkyl group, a -CW3R6 group, a -COCOR7 group, a -NHCOR7 group, a -C(=W3)W4R5 group, a - (NH)m SO2R9 group, a -(NH)m SO2OR10 group or a - (NH)m SO2N(R11)R12 group; each of R1, R6 and R9 is a chain hydrocarbon group, a monocyclic hydrocarbon group, a polycyclic hydrocarbon group, a monocyclic heterocycle group or a polycyclic heterocycle group; each of R2 and R7 is an alkyl group, an alkoxy group, a phenyl group or a phenoxy group; each of R3, R8 and R10 is an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, a phenyl group or a benzyl group; each of R4, R5, R11 and R12 is an alkyl group; each of W1, W2, W3 and W4 is an oxygen atom or a sulfur atom;
and m is 0 or 1.
Claims (8)
1. A therapeutic or preventive agent for digestive system diseases, containing as an active ingredient a diaminotrifluoromethylpyridine derivative represented by the formula (I) or its salt:
wherein X is a -CW1R1 group, a -COCOR2 group, a -CW1NHCOR2 group, a -C(=W1)W2R3 group or a -CW1N(R4)R5 group; Y is an alkyl group, a -CW3R6 group, a -COCOR7 group, a -NHCOR7 group, a -C(=W3)W4R8 group, a -(NH)m SO2R9 group, a - (NH)m SO2OR10 group or a - (NH)m SO2N(R11)R12 group; each of R1, R6 and R9 which are independent of one another, is a chain hydrocarbon group which may be substituted, a monocyclic hydrocarbon group which may be substituted, a polycyclic hydrocarbon group which may be substituted, a monocyclic heterocycle group which may be substituted or a polycyclic heterocycle group which may be substituted;
each of R2 and R7 which are independent of each other, is an alkyl group which may be substituted, an alkoxy group which may be substituted, a phenyl group which may be substituted or a phenoxy group which may be substituted;
each of R3, R8 and R10 which are independent of one another, is an alkyl group which may be substituted, an alkenyl group which may be substituted, an alkynyl group which may be substituted, a cycloalkyl group which may be substituted, a phenyl group which may be substituted or a benzyl group which may be substituted; each of R4, R5, R11 and R12 which are independent of one another, is an alkyl group which may be substituted; each of W1, W2, W3 and W4 which are independent of one another, is an oxygen atom or a sulfur atom; and m is 0 or 1, excluding a case where one of X and Y is a -COCF2X1 group (wherein X1 is a hydrogen atom, a halogen atom, an alkyl group or a haloalkyl group), and the other is a -COCF2X2 group (wherein X2 is a hydrogen atom, a halogen atom, an alkyl group, a haloalkyl group or an alkylcarbonyl group), a -COOX3 group (wherein X3 is an alkyl group which may be substituted or a phenyl group which may be substituted) or a -COX4 group (wherein X4 is an alkyl group, a haloalkyl group, an alkenyl group, an alkynyl group, a phenyl group which may be substituted, a furanyl group or a naphthyl group).
wherein X is a -CW1R1 group, a -COCOR2 group, a -CW1NHCOR2 group, a -C(=W1)W2R3 group or a -CW1N(R4)R5 group; Y is an alkyl group, a -CW3R6 group, a -COCOR7 group, a -NHCOR7 group, a -C(=W3)W4R8 group, a -(NH)m SO2R9 group, a - (NH)m SO2OR10 group or a - (NH)m SO2N(R11)R12 group; each of R1, R6 and R9 which are independent of one another, is a chain hydrocarbon group which may be substituted, a monocyclic hydrocarbon group which may be substituted, a polycyclic hydrocarbon group which may be substituted, a monocyclic heterocycle group which may be substituted or a polycyclic heterocycle group which may be substituted;
each of R2 and R7 which are independent of each other, is an alkyl group which may be substituted, an alkoxy group which may be substituted, a phenyl group which may be substituted or a phenoxy group which may be substituted;
each of R3, R8 and R10 which are independent of one another, is an alkyl group which may be substituted, an alkenyl group which may be substituted, an alkynyl group which may be substituted, a cycloalkyl group which may be substituted, a phenyl group which may be substituted or a benzyl group which may be substituted; each of R4, R5, R11 and R12 which are independent of one another, is an alkyl group which may be substituted; each of W1, W2, W3 and W4 which are independent of one another, is an oxygen atom or a sulfur atom; and m is 0 or 1, excluding a case where one of X and Y is a -COCF2X1 group (wherein X1 is a hydrogen atom, a halogen atom, an alkyl group or a haloalkyl group), and the other is a -COCF2X2 group (wherein X2 is a hydrogen atom, a halogen atom, an alkyl group, a haloalkyl group or an alkylcarbonyl group), a -COOX3 group (wherein X3 is an alkyl group which may be substituted or a phenyl group which may be substituted) or a -COX4 group (wherein X4 is an alkyl group, a haloalkyl group, an alkenyl group, an alkynyl group, a phenyl group which may be substituted, a furanyl group or a naphthyl group).
2. The therapeutic or preventive agent for digestive system diseases according to Claim 1, wherein X is a -CW1R1 group or a -C(=W1)W2R3 group and Y is a -SO2R9 group.
3. The therapeutic or preventive agent for digestive system diseases according to Claim 1, wherein X is a -CW1R1 group or a -C(=W1)W2R3 group, R1 is an alkyl group which may be substituted, an alkenyl group which may be substituted, a cycloalkyl group which may be substituted, a cycloalkenyl group which may be substituted, a phenyl group which may be substituted, a tetrahydronaphthyl group which may be substituted, an indanyl group which may be substituted, a furanyl group which may be substituted or a thienyl group which may be substituted, R3 is an alkyl group which may be substituted, Y is a -SO2R9 group, and R9 is an alkyl group which may be substituted, an alkenyl group which may be substituted, a cycloalkyl group which may be substituted, a cycloalkenyl group which may be substituted or a phenyl group which may be substituted.
4. The therapeutic or preventive agent for digestive system diseases according to Claim 1, wherein X is a -CW1R1 group or a -C(=W1)W2R3 group, R1 is an alkyl group, a haloalkyl group, an alkoxycarbonyl alkyl group, an alkenyl group, a haloalkenyl group, an alkenyl group substituted with a thienyl group, a cycloalkyl group, a cycloalkyl group substituted with a halogen atom, a phenyl group, a phenyl group substituted with a halogen atom, a phenyl group substituted with an alkyl group or a haloalkyl group, a phenyl group substituted with an alkoxy group or a haloalkoxy group, a tetrahydronaphthyl group, an indanyl group, a furanyl group or a thienyl group, R3 is an alkyl group or a haloalkyl group, Y is a -SO2R9 group, and R9 is an alkyl group, a haloalkyl group, a phenyl group, a phenyl group substituted with a halogen atom, a phenyl group substituted with an alkyl group or a haloalkyl group, or a phenyl group substituted with an alkoxy group or a haloalkoxy group.
5. The therapeutic or preventive agent for digestive system diseases according to Claim 1, wherein X is an alkoxycarbonyl alkylcarbonyl group, an alkenylcarbonyl group, an alkenylcarbonyl group substituted with a thienyl group, a cycloalkylcarbonyl group, an indanylcarbonyl group, a furancarbonyl group, a thiophenecarbonyl group, a tetrahydronaphthylcarbonyl group or a benzoyl group which may be substituted with a halogen atom or a haloalkyl group, and Y is an alkylsulfonyl group.
6. The therapeutic or preventive agent for digestive system diseases according to Claim 1, wherein X is a cycloalkylcarbonyl group, a furancarbonyl group or a benzoyl group which may be substituted with halogen, and Y is an alkylsulfonyl group.
7. The therapeutic or preventive agent for digestive system diseases according to Claim 1, wherein the diaminotrifluoromethylpyridine derivative is N-(2-ethylsulfonylamino-5-trifluoromethyl-3-pyridyl)cyclohexane carboxamide, N-(2-methylsulfonylamino-5-trifluoromethyl-3-pyridyl)-4-fluorobenzamide, N-(2-isopropylsulfonylamino-5-trifluoromethyl-3-pyridyl)-3-fluorobenzamide, N-(2-methylsulfonylamino-5-trifluoromethyl-3-pyridyl)-2-furancarboxamide or N-(2-isopropylsulfonylamino-5-trifluoromethyl-3-pyridyl)cyclopentanecarboxamide.
8. The therapeutic or preventive agent for digestive system diseases according to Claim 1, wherein the diaminotrifluoromethylpyridine derivative is N-(2-ethylsulfonylamino-5-trifluoromethyl-3-pyridyl)cyclohexane carboxamide.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2000-22817 | 2000-01-31 | ||
| JP2000022817 | 2000-01-31 | ||
| PCT/JP2001/000614 WO2001056568A1 (en) | 2000-01-31 | 2001-01-30 | Remedies or preventives for digestive diseases containing diaminotrifluoromethylpyridine derivatives |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2398898A1 true CA2398898A1 (en) | 2001-08-09 |
| CA2398898C CA2398898C (en) | 2010-03-30 |
Family
ID=18549065
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2398898A Expired - Lifetime CA2398898C (en) | 2000-01-31 | 2001-01-30 | Therapeutic or preventive agent for digestive system diseases containing a diaminotrifluoromethylpyridine derivative |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US6653333B2 (en) |
| EP (1) | EP1252890B1 (en) |
| KR (1) | KR20020070525A (en) |
| CN (1) | CN1277539C (en) |
| AT (1) | ATE399550T1 (en) |
| AU (1) | AU778111B2 (en) |
| CA (1) | CA2398898C (en) |
| DE (1) | DE60134626D1 (en) |
| ES (1) | ES2307626T3 (en) |
| IL (2) | IL150965A0 (en) |
| NZ (1) | NZ520353A (en) |
| RU (1) | RU2266114C2 (en) |
| TW (1) | TWI283578B (en) |
| WO (1) | WO2001056568A1 (en) |
| ZA (1) | ZA200205962B (en) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2003277537A1 (en) * | 2002-10-30 | 2004-05-25 | Ishihara Sangyo Kaisha, Ltd. | REGULATION OF INTERACTION BETWEEN RAPL AND Rap1 |
| CA2635392C (en) * | 2005-12-27 | 2013-07-23 | Universidad Del Pais Vasco - Euskal Herriko Unibertsitatea | New pyrrolic derivatives with histone deacetylase inhibitory activity |
| JP5584518B2 (en) | 2009-05-28 | 2014-09-03 | 石原産業株式会社 | Anti-shock agent containing diaminotrifluoromethylpyridine derivative |
| RU2504779C1 (en) * | 2012-10-08 | 2014-01-20 | Государственное бюджетное образовательное учреждение высшего профессионального образования "Ростовский государственный медицинский университет" Минздравсоцразвития России | Method for evaluating clinical effectiveness in ulcerative colitis |
| CA2959414C (en) | 2014-09-05 | 2023-03-14 | Symbiomix Therapeutics, Llc | Secnidazole for use in the treatment of bacterial vaginosis |
| RU2607160C2 (en) * | 2015-04-27 | 2017-01-10 | Ирина Вадимовна Козлова | Method of treating complications in patients with chronic nonspecific ulcerative colitis |
| CA2988082C (en) * | 2015-06-01 | 2020-09-29 | Symbiomix Therapeutics, Llc | Novel nitroimidazole formulations and uses thereof |
| JP2018177701A (en) * | 2017-04-14 | 2018-11-15 | エーザイ・アール・アンド・ディー・マネジメント株式会社 | Pharmaceutical composition for treating crohn's disease |
| AU2018361503A1 (en) | 2017-11-02 | 2020-05-14 | Ishihara Sangyo Kaisha, Ltd. | Sustained-release medical composition |
| BR112020016515A2 (en) | 2018-03-01 | 2020-12-15 | Ishihara Sangyo Kaisha, Ltd. | PHARMACEUTICAL COMPOSITION WITH EXCELLENT STORAGE STABILITY |
| US12473259B2 (en) | 2019-05-15 | 2025-11-18 | Ishihara Sangyo Kaisha, Ltd. | Anhydrous crystal of monosodium n-(2-ethylsulfonylamino-5-trifluoromethyl-3-pyridyl)cyclohexane carboxamide |
| US12280037B2 (en) | 2020-09-22 | 2025-04-22 | Evofem Biosciences, Inc. | Method and pharmaceutical composition for treating or preventing trichomoniasis and uses thereof |
| RS67285B1 (en) * | 2020-09-29 | 2025-11-28 | Ishihara Sangyo Kaisha | Liquid pharmaceutical composition demonstrating excellent preservation efficacy |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5229403A (en) | 1990-07-10 | 1993-07-20 | Ishihara Sangyo Kaisha Ltd. | Diaminotrifluoromethylpyridine derivatives and phospholipase A2 inhibitor containing them |
| JPH07126189A (en) | 1993-09-09 | 1995-05-16 | Takeda Chem Ind Ltd | Preparation for combined antiulcer treatment |
| JPH08259447A (en) | 1995-03-24 | 1996-10-08 | Takeda Chem Ind Ltd | Chlcystokinin antagonistic agent |
| JP3183378B2 (en) | 1995-06-28 | 2001-07-09 | 参天製薬株式会社 | Mucin production promoter |
| JPH09157182A (en) | 1995-12-06 | 1997-06-17 | Hoechst Japan Ltd | New therapeutic agent for ulcerative colitis |
| JPH10101576A (en) | 1996-10-01 | 1998-04-21 | Nisshin Flour Milling Co Ltd | Treating medicine for digestive organ disease |
| JPH10167985A (en) | 1996-10-08 | 1998-06-23 | Takeda Chem Ind Ltd | Anti-helicobacter pylori agent |
| ZA981430B (en) | 1997-02-28 | 1998-08-24 | Ishihara Sangyo Kaisha | Anticancer composition |
| JPH10330346A (en) | 1997-05-28 | 1998-12-15 | Daiichi Rajio Isotope Kenkyusho:Kk | Straight chain nitrone derivative and pharmaceuticals and reagents containing the same |
| JPH1112171A (en) | 1997-06-19 | 1999-01-19 | Nisshin Flour Milling Co Ltd | Therapeutic agent for digestive system disease |
| JPH1192373A (en) | 1997-09-24 | 1999-04-06 | Taisho Pharmaceut Co Ltd | Gastric mucosa protective agent |
-
2001
- 2001-01-30 NZ NZ520353A patent/NZ520353A/en not_active IP Right Cessation
- 2001-01-30 CN CNB018043054A patent/CN1277539C/en not_active Expired - Fee Related
- 2001-01-30 KR KR1020027009789A patent/KR20020070525A/en not_active Ceased
- 2001-01-30 DE DE60134626T patent/DE60134626D1/en not_active Expired - Lifetime
- 2001-01-30 RU RU2002123373/15A patent/RU2266114C2/en not_active IP Right Cessation
- 2001-01-30 EP EP01948937A patent/EP1252890B1/en not_active Expired - Lifetime
- 2001-01-30 AT AT01948937T patent/ATE399550T1/en not_active IP Right Cessation
- 2001-01-30 ES ES01948937T patent/ES2307626T3/en not_active Expired - Lifetime
- 2001-01-30 IL IL15096501A patent/IL150965A0/en active IP Right Grant
- 2001-01-30 TW TW090101811A patent/TWI283578B/en not_active IP Right Cessation
- 2001-01-30 AU AU28861/01A patent/AU778111B2/en not_active Ceased
- 2001-01-30 WO PCT/JP2001/000614 patent/WO2001056568A1/en not_active Ceased
- 2001-01-30 US US10/182,374 patent/US6653333B2/en not_active Expired - Lifetime
- 2001-01-30 CA CA2398898A patent/CA2398898C/en not_active Expired - Lifetime
-
2002
- 2002-07-25 ZA ZA200205962A patent/ZA200205962B/en unknown
- 2002-07-29 IL IL150965A patent/IL150965A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| TWI283578B (en) | 2007-07-11 |
| CN1400900A (en) | 2003-03-05 |
| ATE399550T1 (en) | 2008-07-15 |
| US6653333B2 (en) | 2003-11-25 |
| CA2398898C (en) | 2010-03-30 |
| IL150965A0 (en) | 2003-02-12 |
| RU2266114C2 (en) | 2005-12-20 |
| ZA200205962B (en) | 2003-08-18 |
| AU778111B2 (en) | 2004-11-18 |
| CN1277539C (en) | 2006-10-04 |
| EP1252890A4 (en) | 2003-05-07 |
| IL150965A (en) | 2008-06-05 |
| RU2002123373A (en) | 2004-03-10 |
| KR20020070525A (en) | 2002-09-09 |
| AU2886101A (en) | 2001-08-14 |
| DE60134626D1 (en) | 2008-08-14 |
| ES2307626T3 (en) | 2008-12-01 |
| NZ520353A (en) | 2005-02-25 |
| WO2001056568A1 (en) | 2001-08-09 |
| US20030027843A1 (en) | 2003-02-06 |
| EP1252890B1 (en) | 2008-07-02 |
| EP1252890A1 (en) | 2002-10-30 |
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